6-(4-Chlorobenzyl)-9-(cyclopropylmethyl)-8,9,10,11-tetrahydropyrido[4',3':4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]-pyrimidin-5(6H)-one

ID: ALA4086861

PubChem CID: 118485600

Max Phase: Preclinical

Molecular Formula: C21H20ClN5OS

Molecular Weight: 425.95

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1n(Cc2ccc(Cl)cc2)c2sc3c(c2c2ncnn12)CCN(CC1CC1)C3

Standard InChI:  InChI=1S/C21H20ClN5OS/c22-15-5-3-14(4-6-15)10-26-20-18(19-23-12-24-27(19)21(26)28)16-7-8-25(9-13-1-2-13)11-17(16)29-20/h3-6,12-13H,1-2,7-11H2

Standard InChI Key:  KGQCLTUHOICIST-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 34  0  0  0  0  0  0  0  0999 V2000
   14.8771  -17.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5846  -18.0439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5814  -18.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8707  -19.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1632  -18.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1623  -18.0383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3628  -17.7922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8445  -18.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3617  -19.1188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6968  -20.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8819  -20.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5505  -19.4051    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.5487  -20.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1785  -20.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8453  -21.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0263  -21.5689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8762  -16.8112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6931  -22.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1706  -22.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2556  -23.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9208  -23.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4548  -17.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4580  -16.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1687  -16.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1719  -15.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4603  -15.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7496  -15.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7464  -16.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4635  -14.3467    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  8  9  1  0
  2  7  1  0
  3  9  2  0
 10 11  2  0
 11 12  1  0
 14 15  1  0
 15 16  1  0
 13 16  1  0
 10 14  1  0
 11 13  1  0
  4 10  1  0
  5 12  1  0
  1 17  2  0
 19 20  1  0
 20 21  1  0
 19 21  1  0
 18 19  1  0
 16 18  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 23 28  2  0
 26 29  1  0
  6 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086861

   US10092575, Example 103

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 425.95

Molecular Weight (Monoisotopic): 425.1077

AlogP: 3.58

#Rotatable Bonds: 4

Polar Surface Area: 55.43

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.01

CX LogP: 4.27

CX LogD: 4.12

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -2.01

References

1. Dyck B, Branstetter B, Gharbaoui T, Hudson AR, Breitenbucher JG, Gomez L, Botrous I, Marrone T, Barido R, Allerston CK, Cedervall EP, Xu R, Sridhar V, Barker R, Aertgeerts K, Schmelzer K, Neul D, Lee D, Massari ME, Andersen CB, Sebring K, Zhou X, Petroski R, Limberis J, Augustin M, Chun LE, Edwards TE, Peters M, Tabatabaei A..  (2017)  Discovery of Selective Phosphodiesterase 1 Inhibitors with Memory Enhancing Properties.,  60  (8): [PMID:28406621] [10.1021/acs.jmedchem.7b00302]

Source

Source(1):

• Scientific Literature